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3-n-butyl-1-isoindolinone and use thereof for preventing or treating cerebral infarction

a technology of n-butylphthalide and isoindolinone, which is applied in the direction of biocide, drug composition, extracellular fluid disorder, etc., can solve the problems of serious limitations in applications, achieve broad selective dosage range, overcome the shortcomings of butylphthalide preparations, and reduce the effect of medicine cos

Active Publication Date: 2015-07-02
SUN YAT SEN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent text discusses the use of a compound called 3-n-butyl-1-isoindolinone for treating cerebral ischemia. This compound has a more solid structure than the currently used butylphthalide, which makes it easier to prepare and administer. It has also been shown to have good efficacy in treating cerebral ischemia. This compound has the potential to decrease pharmaceutical costs and improve drug efficiency. Overall, this patent aims to provide a new treatment option for cerebral ischemia and to improve the overall production and cost-effectiveness of this compound.

Problems solved by technology

However, butylphthalide is an oily liquid and is water insoluble; as a result, it can only be prepared in the form of oil-soluble liquid preparations, which seriously limits the applications thereof.

Method used

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  • 3-n-butyl-1-isoindolinone and use thereof for preventing or treating cerebral infarction
  • 3-n-butyl-1-isoindolinone and use thereof for preventing or treating cerebral infarction
  • 3-n-butyl-1-isoindolinone and use thereof for preventing or treating cerebral infarction

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of 3-n-butyl-1-isoindolinone (NBI)

[0042]The objective product is obtained using Grignard reagent reduction method by two-step reaction. First, phthalimide is selected as a starting reactant, and a nucleophilic Grignard reagent, i.e., butyl magnesium bromide, is used to realize addition of an alkyl group of a carbonyl carbon of an amide bond, thereby yielding an intermediate. Second, boron trifluoride diethyl etherate is used as a catalyst and triethylsilane is used as a reductant to remove an oxygen atom from a third carbon atom, thereby obtaining a deoxidized product, i. e., NBI. The compound is purified by multiple times recrystallization, and structure of the compound is confirmed by mass spectrum (MS) and nuclear magnetic resonance (1H-NMR, 13C-NMR). The synthesis flow chart of NBI is summarized as follows:

[0043]1. Preparation of Grignard Reagent Butyl Magnesium Bromide

[0044]Magnesium powder (approximately 0.240 g, 10 mmol) is accurately weighed and added to a dried 10...

example 2

Preparation of Tablets of 3-n-butyl-1-isoindolinone

[0051]

Prescription3-n-butyl-1-isoindolinone20gStarch20gEthanol (50 v. %)proper amountSodium carboxymethyl starch3gmagnesium stearate0.3g200tablets

[0052]3-n-butyl-1-isoindolinone is collected at an accurately constant weight according to the prescription, ground into powder, and screened by a 100-mesh sieve. Starch is collected at an accurately constant weight and screened by the 100-mesh sieve. 3-n-butyl-1-isoindolinone and starch after screening are evenly mixed, and a proper amount of 50 v. % of ethanol is added to a resulting mixture to prepare a damp mass. An 18-mesh nylon sieve is used for granulation. Granules are dried at a temperature of between 60 and 70° C. The 18-mesh sieve is then used for shaping the granules. After that, sodium carboxymethyl starch and magnesium stearate are added and evenly mixed. A φ8 mm press die is used to prepare tablets.

example 3

Preparation of Hard Capsules of 3-n-butyl-1-isoindolinone

[0053]

Prescription3-n-butyl-1-isoindolinone20gStarch20gEthanol (50 v. %)proper amountSodium carboxymethyl starch3gmagnesium stearate0.3g200capsules

[0054]The wet granulation method herein is the same as that in Example 1. 3-n-butyl-1-isoindolinone is collected at an accurately constant weight according to the prescription, ground into powder, and screened by a 100-mesh sieve. Starch is collected at an accurately constant weight and screened by the 100-mesh sieve. 3-n-butyl-1-isoindolinone and starch after screening are evenly mixed, and a proper amount of 50 v. % of ethanol is added to a resulting mixture to prepare a damp mass. An 18-mesh nylon sieve is used for granulation. Granules are dried at a temperature of between 60 and 70° C. The 18-mesh sieve is used for shaping the granules. After that, contents of ingredients are measured, and qualified granules are encapsulated into number 1 capsules.

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Abstract

3-n-Butyl-1-isoindolinone and use thereof for preventing or treating cerebral infarction. The compound is prepared by: 1) employing phthalimide as a starting reactant, contacting a nucleophilic Grignard reagent with the original reactant to add an alkyl group to a carbonyl carbon of an amide bond of the original reactant, thus yielding an intermediate; and 2) removing an oxygen atom connected to a third carbon atom of the intermediate in the presence of boron trifluoride diethyl etherate as a catalyst and triethylsilane as a reductant.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application is a continuation-in-part of International Patent Application No. PCT / CN2013 / 083237 with an international filing date of Sep. 10, 2013, designating the United States, now pending, and further claims priority benefits to Chinese Patent Application No. 201210341648.6 filed Sep. 14, 2012. The contents of all of the aforementioned applications, including any intervening amendments thereto, are incorporated herein by reference. Inquiries from the public to applicants or assignees concerning this document or the related applications should be directed to: Matthias Scholl P.C., Attn.: Dr. Matthias Scholl Esq., 245 First Street, 18th Floor, Cambridge, Mass. 02142.BACKGROUND OF THE INVENTION[0002]1. Field of the Invention[0003]The invention belongs to 3-n-butyl-1-isoindolinone and the use thereof in preparation of drugs for preventing or treating cerebral infarction.[0004]2. Description of the Related Art[0005]Cerebral infarction ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D209/46
CPCC07D209/46A61P7/02A61P9/10A61K31/4035
Inventor ZHAO, CHUNSHUNXU, WENKAI
Owner SUN YAT SEN UNIV
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